Sodium Bicarbonate → HCID 66603654, compound

HRID 403566Notes

Reaction equation

HRID 403566 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[NH2:18][C:19]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH3:36][C:34]([CH3:37])([O:33][C:31]([NH:30][CH2:29][C:26]1[CH:27]=[CH:28][C:19]([NH:18][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]2)=[C:20]([C:21]([O:23][CH3:24])=[O:22])[CH:25]=1)=[O:32])[CH3:35]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 643496Benzyl 4-oxopiperidine-1-carboxylate2×HCID 5049666Sodium triacetoxyborohydride2×HCID 60103040Methyl 2-amino-5-((((tert-butoxy)carbonyl)amino)methyl)benzoate

Product 1

HCID 66603654HCID 66603654, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.66 g of benzyl 4-oxopiperidine-1-carboxylate and 1 g of methyl 2-amino-5-({[(1,1-dimethylethoxy)carbonyl]amino}methyl)benzoate obtained in stage 5.1 in 20 ml of DCM is added dropwise at AT to a suspension of 2.04 g of NaBH(OAc)3 in a mixture of 20 ml of DCM and 0.41 ml of AcOH. The mixture is stirred at AT for 15 h 00 and then a further 2.04 g of NaBH(OAc)3 are added. After stirring for 6 h 00, 1.66 g of benzyl 4-oxopiperidine-1-carboxylate are added and the mixture is stirred at AT for 48 h 00. A saturated NaHCO3 solution is added and extraction is carried out with DCM. The organic phase is washed with a saturated NaHCO3 solution and twice with a saturated NH4Cl solution. It is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (5/95, v/v) as far as (40/60, v/v), to give 1.6 g of the expected product.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at AT for 48 h 00
  3. extractionextraction
  4. washThe organic phase is washed with a saturated NaHCO3 solution and twice with a saturated NH4Cl solution
  5. dry with materialIt is dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-88eb812eef38463187e8e11be5924365
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Reaction notes

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